The most controversial figure to profit from Facebook's IPO last month was Peter Thiel, already rich from founding PayPal. Thiel was the first outside investor in Facebook and looks likely to make at least a cool $1.5 billion from his 2.5% stake. (Read Peter Thiel's IP profile).

To understand Thiel's perspective, it helps to understand his ideology. But trying to summarize Thiel's philosophy is a challenge; Thiel is known as a libertarian, but that's not quite right. Thiel believes in complete and unadulterated "freedom," combined with a relentless belief in technological progress. He's an Ayn Randian but also an Asimovian. He believes in science fiction as aspiration, rejects the iPhone as mundane, and tries to always be one step ahead of the herd. In a fascinating profile in the New Yorker, Thiel claims that "as an investor-entrepreneur, I've always tried to be contrarian, to go against the crowd, to identify opportunities in places where people are not looking."

Thiel’s most controversial project, and one that’s emblematic of Thiel's investing, has been his famous Thiel Fellowships, 22 grants of $100,000 each for promising college students to drop out and start their own businesses. Thiel believes that higher education, much like the housing sector, is a bubble. It has stopped providing a valuable social good and is instead a place where the elite send their children to maintain their status. To disrupt higher education's monopoly on the best and brightest, Thiel wants to attract them to innovate now.

Thiel's perspective guides his investing, as he urges radicalism in funding new enterprises. To that end he extensively funds breakthrough technologies. He tries to avoid "extensive" progress, to take what's working and improve it, and funds "intensive" progress, starting something entirely new. That helps to explain Thiel's enthusiasm for Facebook, PayPal, and other successful (and not so successful) startups that he’s funded. They’re unique. When funding philanthropy, Thiel tries to anticipate the future.

Thiel clearly approaches philanthropy with a venture capitalist's perspective. In the same New Yorker profile, he illuminated his perspective, advising a man who wanted to found a nonprofit to avoid falling into the trap of thinking that "it’s not about making money, we’re doing something good, so we don’t have to work as hard."